Composition for reducing malodor and use thereof

Abstract

The present disclosure generally provides taste-modifying compositions that reduce the off-odor of alkali metal salts of peroxymonosulfuric acid. In some aspects, the present disclosure provides the use of such taste-modifying compositions to reduce the off-odor of alkali metal salts of peroxymonosulfuric acid, such as potassium peroxymonosulfate. In some other aspects, the present disclosure provides compositions (e.g., oral care compositions) comprising an alkali metal salt of peroxymonosulfuric acid and a taste-modifying composition of the present disclosure. In some embodiments, such compositions are in the form of an oral care product (e.g., a toothpaste, a mouthwash, etc.).

Description

[0001] Cross-reference to related applications

[0002] This application claims priority to U.S. Provisional Application No. 63 / 034,095, filed June 3, 2020, and European Patent Application No. 20179560.6, filed June 11, 2020, both of which are incorporated herein by reference as if they were set forth in their entirety. Technical Field

[0003] This disclosure generally provides taste-modifying compositions for reducing the odor of alkali metal salts of persulfate. In some forms, this disclosure provides the use of such taste-modifying compositions for reducing the odor of alkali metal salts of persulfate, such as potassium persulfate. In other forms, this disclosure provides compositions (e.g., edible compositions or oral care compositions) comprising an alkali metal salt of persulfate and the taste-modifying compositions of this disclosure. In some embodiments, such compositions are in the form of oral care products (e.g., toothpaste, mouthwash, teeth whitening compositions, etc.). Background Technology

[0004] The taste system provides sensory information about the chemical composition of the external world. Taste transduction is one of the more complex forms of chemically triggered sensation in animals. Taste signals can be found throughout the animal kingdom, from simple metazoans to the most complex vertebrates. Mammals are believed to have five basic forms of taste: sweet, bitter, sour, salty, and umami.

[0005] Alkali metal salts, such as potassium persulfates, are commonly used as whitening agents in oral care products. The presence of such salts can cause unpleasant odors. Limiting the concentration of these salts is a potential strategy to reduce any unpleasant taste. However, it may often be necessary to include these salts at higher concentrations to achieve a better effect.

[0006] Therefore, there is a need to discover new compositions that can effectively reduce the odor perception experienced by humans associated with alkali metal salts of persulfate. Summary of the Invention

[0007] This disclosure relates to the discovery that certain compositions exhibit unexpected effectiveness in reducing the perception of saltiness caused by the presence of sodium cations in oral care products.

[0008] In a first embodiment, this disclosure provides a flavor-enhancing composition comprising: (a) 4-amino-5,6-dimethylthieno[2,3-d]pyrimidine-2(1H)-one, or a salt thereof; and (b) a lactone. In some embodiments, the composition comprises a sweetener, such as sucralose. In some further embodiments, the composition comprises glucosylated natural steviol glycoside. In some further embodiments, the composition comprises a flavoring agent.

[0009] In a second embodiment, this disclosure provides the use of the flavor-modifying composition of the first embodiment for reducing the off-flavors of flavored products. In some embodiments, the flavored product is an oral care product, such as toothpaste, mouthwash, or teeth whitening composition.

[0010] In a third embodiment, this disclosure provides a method for reducing the off-flavor of a flavored product, the method comprising introducing a flavor-modifying composition of the first embodiment into the flavored product. In some embodiments, the flavored product is an oral care product, such as toothpaste, mouthwash, or teeth whitening product. In some embodiments, the flavored product comprises an alkali metal salt of persulfate, such as potassium persulfate.

[0011] In a fourth embodiment, this disclosure provides a flavored product comprising the flavor-modifying composition of the first embodiment and containing an alkali metal salt of persulfate, such as potassium persulfate. In some embodiments, the flavored product is an oral care product, such as toothpaste, mouthwash, or teeth whitening product.

[0012] Further forms and embodiments thereof are set forth in the following detailed description, figures, abstract and claims. Detailed Implementation

[0013] The following detailed description illustrates the various forms and implementations provided herein. This description is intended for reading by a person skilled in the art. Therefore, information familiar to such a person may not be included.

[0014] definition

[0015] Unless otherwise specified herein, the following terms and phrases have the meanings indicated below. This disclosure may employ other terms and phrases not expressly defined herein. Such other terms and phrases have the meanings that those skilled in the art would have in the context of this disclosure. In some cases, a term or phrase may be defined in a singular or plural form. In such cases, it should be understood that any term in its singular form may include its plural form, and vice versa, unless the contrary is explicitly stated.

[0016] In this article, “sweetener,” “sweetener,” “sweetener entity,” or “sweetener compound” means a compound that produces a detectable sweetness in a subject or an ingestible salt thereof, such as a compound that activates the T1R2 / T1R3 receptor in vitro.

[0017] "Odor" refers to a taste that is generally considered unpleasant by humans, such as bitterness, metallic taste, burning taste, aldehyde taste, or any combination thereof.

[0018] As used herein, the singular forms “an,” “a,” and “the” include plural indicators unless the context clearly indicates otherwise. For example, reference to “an substituent” covers a single substituent as well as two or more substituents, and so on.

[0019] As used herein, the words “for example,” “such as,” “like,” or “including” are intended to introduce examples that further illustrate a more general subject. Unless otherwise expressly stated, such examples are provided only to aid in understanding the embodiments shown in this disclosure and are not intended to be limiting in any way. These phrases also do not indicate any kind of preference for the disclosed embodiments.

[0020] As used herein, “include,” “contain,” “with,” and “comprised of” refer to an open group, meaning that the group may include other members besides those explicitly stated. For example, the phrase “includes A” means that A must be present, but other members may also be present. The terms “include,” “have,” and “composed of,” and their grammatical variations, have the same meaning. Conversely, “consist of,” “formed by,” or “constituting as” refer to a closed group. For example, the phrase “composed of A” means that only A exists.

[0021] As used herein, "optionally" means that the events described below may or may not occur. In some embodiments, the optional event does not occur. In other embodiments, the optional event does occur one or more times.

[0022] As used herein, “or” will be given its broadest reasonable interpretation and is not limited to the “either / or” construction. Therefore, the phrase “containing A or B” means that A may exist while B does not, or B may exist while A does not, or both A and B may exist. Furthermore, for example, if A defines a class that can have multiple members (e.g., A1 and A2), then one or more members of that class may exist simultaneously.

[0023] Other terms are defined in other parts of this specification, even if not included in this subsection.

[0024] Flavor-improving compositions

[0025] In at least one embodiment, this disclosure provides a flavor-modifying composition comprising: (a) 4-amino-5,6-dimethylthiopheno[2,3-d]pyrimidine-2(1H)-one, or a salt thereof; and (b) a lactone.

[0026] As described above, the flavor-modifying compositions that can be used contain 4-amino-5,6-dimethylthiopheno[2,3-d]pyrimidine-2(1H)-one or any suitable salt thereof. In some embodiments, the flavor-modifying compositions disclosed herein contain the hydrochloride salt of 4-amino-5,6-dimethylthiopheno[2,3-d]pyrimidine-2(1H)-one.

[0027] The flavor-modifying composition also contains a lactone. Any suitable lactone or a combination of lactones can be used. In some embodiments, the lactone comprises a lactone ring having 3 to 8 members, such as a 3-membered, 4-membered, 5-membered, 6-membered, 7-membered, or 8-membered lactone ring.

[0028] In some embodiments, the lactone comprises a 5-membered lactone ring having or not having unsaturated bonds (excluding the degree of unsaturation in the oxygen substituents on the ring), such as carbon-carbon double bonds. In some embodiments, the lactone comprises a 5-membered lactone ring having at least one unsaturated bond (e.g., one carbon-carbon double bond). Non-limiting examples of lactones comprising a 5-membered lactone ring having at least one unsaturated bond include angelicin α, angelicin β, menthol, 5,5-dimethyl-2(5H)-furanone, 5-ethyl-2(5H)-furanone, 5-pentyl-2(5H)-furanone, 5-hexyl-2(5H)-furanone, 5-pentyl-2(3H)-furanone, 4-methyl-3-pentyl-2(5H)-furanone, and 2(5H)-furanone. In some embodiments, the lactone comprises a 5-membered lactone ring without any unsaturated bonds. Non-limiting examples of such lactones include butyrolactoneγ, valproiconeγ, caprolactoneγ, heptanolactoneγ, octylolactoneγ, undecylolactoneγ, decylolactoneγ, dihydrojasmone lactone, and dihydromenthide lactone (3,6-dimethyl-hexahydro-2(3H)-benzofuranone). In some embodiments, the lactone is dihydromenthide lactone.

[0029] In some embodiments, the lactone comprises a 6-membered lactone ring with or without unsaturated bonds. In some embodiments, the lactone comprises a 6-membered lactone ring having at least one unsaturated bond. Non-limiting examples of lactones comprising a 6-membered lactone ring having at least one unsaturated bond include δ-2-decenolactone, coumarin, and 6-methylcoumarin. In some other embodiments, the lactone comprises a 6-membered lactone ring without any unsaturated bonds. Non-limiting examples of lactones comprising a 6-membered lactone ring without any unsaturated bonds include decanolide δ, dodecalide δ, and cyclohexyllactone.

[0030] Flavor-improving compositions may include certain additional ingredients. For example, in some embodiments, the flavor-improving composition comprises: (c) glucosylated natural steviol glycosides. As used herein, the term "natural steviol glycoside" refers to steviol glycosides naturally occurring in the plant species Stevia rebaudiana, Stevia phlebophylla, or Rubus chingii. Such compounds are glycosides of diterpenoid steviols. Some non-limiting examples include steviol glycosides, rebaudioside A, rebaudioside C, dulcitoside A, etc. As used herein, the term "glucosylated natural steviol glycoside" refers to a compound obtained by enzymatically glucosylating a natural steviol glycoside to increase the degree of glucosylation. As used herein, the term "GSG" may be used interchangeably with "glucosylated natural steviol glycoside".

[0031] In embodiments where GSG is present, any suitable GSG can be used. Therefore, the GSG can have any suitable degree of additional glucosylation, and any suitable type of glucosylation. In some embodiments, the GSG used in the flavor-improving composition has a glucosylation degree of at least 1.0, meaning that at least one mole of glucose has been enzymatically added to the natural steviol glycoside for every mole of natural steviol glycoside. In some other embodiments, the GSG used in the flavor-improving composition has a glucosylation degree of at least 1.1, or at least 1.2, or at least 1.3, or at least 1.4, or at least 1.5, or at least 1.6, or at least 1.7, or at least 1.8, or at least 1.9, or at least 2.0, or at least 2.1, or at least 2.2, or at least 2.3, or at least 2.4, or at least 2.5. Gluosylation can be of any suitable type. For example, in some embodiments, the glucose enzymatically added to the natural steviol glycoside is α-glucose, β-glucose, or a combination thereof. In some embodiments, the glucose added enzymatically to the natural steviol glycoside is α-glucose. In some embodiments, the glucose added enzymatically to the natural steviol glycoside is β-glucose. In some embodiments, the glucose added enzymatically to the natural steviol glycoside is a combination of α-glucose and β-glucose. The glucose added via enzymatic glucosylation can be incorporated through any suitable linkage. Typically, the added glucose unit is linked to other glucose units already present on the natural steviol glycoside. In some embodiments, the enzymatically added glucose unit is added via a 1,6 bond, meaning the glucose unit is added via the 1-position of the added glucose unit and the 6-position of a glucose unit already present on the natural steviol glycoside. In some other embodiments, the enzymatically added glucose unit is added via a 1,4 bond. In some other embodiments, the enzymatically added glucose unit is added via a 1,2 bond.

[0032] In some embodiments, the flavor-modifying composition comprises: (d) a sweetener, such as a low-calorie or zero-calorie sweetener. Examples of suitable sweeteners are described in more detail below. In some embodiments, the sweetener is sucralose, which refers to 1,6-dichloro-1,6-dideoxy-β-D-fructofuranosyl-4-chloro-4-deoxy-α-D-galactopyranoside.

[0033] The compounds in groups (a), (b), (c), and (d) may be present in the flavor-modifying composition in any suitable proportions. In some embodiments where both group (a) and group (b) compounds are present, the weight-to-weight ratio of group (a) and group (b) compounds is in the range of 1:1 to 5:1, or 2:1 to 4:1. In some embodiments where both group (a) and group (c) compounds are present, the weight-to-weight ratio of group (a) and group (c) compounds is in the range of 0.8:1.0 to 2.4:1.0, or 1.2:1.0 to 2.0:1.0. In some embodiments where both group (a) and group (d) compounds are present, the weight-to-weight ratio of group (a) and group (d) compounds is in the range of 1:12 to 1:3, or 1:8 to 1:4. In some embodiments where both class (b) and class (c) compounds are present, the weight-to-weight ratio of class (b) and class (c) compounds is in the range of 1:4 to 3:2, or 1:3 to 1:1. In some embodiments where both class (b) and class (d) compounds are present, the weight-to-weight ratio of class (b) and class (d) compounds is in the range of 1:40 to 1:10, or 1:30 to 1:12. In some embodiments where both class (c) and class (d) compounds are present, the weight-to-weight ratio of class (c) and class (d) compounds is in the range of 1:25 to 1:2, or 1:20 to 1:5.

[0034] Flavor-modifying compositions may contain other suitable ingredients, such as additional sweeteners, flavorings, carriers, binders, cooling agents, etc.

[0035] For example, in some embodiments, the flavor-modifying composition comprises caloric sugars such as sucrose, glucose, fructose (e.g., in the form of high-fructose corn syrup), or any combination thereof. In some embodiments, the flavor-modifying composition comprises one or more rebaudine glycosides (e.g., rebaudine A, rebaudine D, rebaudine E, rebaudine M, or any combination thereof). Generally, the concentration of rebaudine glycosides (e.g., rebaudine A) will be about 20 to 50 times higher than the concentration of sucralose described above. In some embodiments, the flavor-modifying composition comprises one or more high-intensity artificial sweeteners, such as acesulfame potassium, aspartame, cyclamate, neotame, etc. When any such high-intensity artificial sweeteners are present in the flavor-modifying composition, their concentration will be approximately the same as the concentration of sucralose described above. In some other embodiments, the flavor-modifying composition comprises one or more low-caloric carbohydrates or sugar alcohols, such as allulose, xylitol, erythritol, etc. In some other embodiments, the flavor-improving composition comprises mogrosides, such as monk fruit juice or extract, or mogroside III, mogroside IV, mogroside V, symmonoside I, isomogroside V, or mogroside IV. E Isomogroside IV E Isomogroside IV and mogroside III E One or more of the 1,6-α isomers of 1,1-oxomogroside V and symmenidine I, and any combination thereof. Other mogroside compounds that may be suitably included in flavor-modifying compositions are described in U.S. Patent Application Publication No. 2017 / 0119032.

[0036] Various other sweeteners may also be included in the flavor-modifying composition. Non-limiting examples include D-allulose, L-ribose, D-tagatose, L-glucose, L-fucose, L-arabinose, D-minobiose, D-leucobionic acid, isomaltitol, lactitol, mannitol, sorbitol, maltodextrin, saccharin, alitane, cyclamic acid, tagatose, maltose, galactose, mannose, lactose, D-tryptophan, glycine, maltitol, lactitol, isomaltitol, hydrogenated starch hydrolysate (HSH), chemically modified mogrosides (such as glucosylated mogroside), carrelame and other guanidine sweeteners, honey, Jerusalem artichoke syrup, licorice root, monk fruit (fruit, powder or extract), lucuma (fruit, powder or extract), maple sap (including, for example, from sugar maple). Sap from various trees including: saccharum, black maple (Acer nigrum), American red maple (Acer rubrum), silver maple (Acersaccharinum), Norway maple (Acer platanoides), ash-leaved maple (Acer negundo), large-leaved maple (Acer macrophyllum), coarse-toothed maple (Acer grandidentatum), Rocky Mountain maple (Acer glabrum), and maple (Acermono); maple syrup; maple sugar; walnut sap (including, for example, sap extracted from white walnut (Juglans cinerea), black walnut (Juglans nigra), ghost walnut (Juglans ailatifolia), and walnut (Juglans regia); and birch sap (including, for example, sap extracted from paper birch (Betula papyrifera), Canadian yellow birch (Betula alleghaniensis), mountain birch (Betula lenta), river birch (Betula nigra), grey birch (Betula populifolia), and weeping birch (Betula...). Resin extracted from *Pendula*, sycamore sap (e.g., sap extracted from *Platanus occidentalis*), ironwood sap (e.g., sap extracted from *Ostrya virginiana*), unrefined sucrose (mascobado), molasses (e.g., blackstrap molasses), molasses sugar, monalose, monellin, cane sugar (cane sugar)Sugar (also known as natural sugar, unrefined sucrose, or cane sugar), palm sugar, panocha, piloncillo, rapadura, raw sugar, rice syrup, sorghum, sorghum syrup, cassava syrup (also known as cassava starch syrup), thaumatin, yacon root, malt syrup, barley malt syrup, barley malt powder, beet sugar, cane sugar Sugar), crystallized fruit juice crystals, caramel, carob syrup, castor oil, hydrogenated starch hydrosol, hydrolyzed canned fruit juice, hydrolyzed starch, invert sugar, anethole, arabinogalactan, concentrated grape juice, syrup, P-4000, acesulfame potassium (also known as acetylsupan potassium or ace-K), aclame, advans, aspartame, baiyunosdie, neotame, benzamide derivatives, bernadame, aspartame alias (canderel), carrelame and other guanidine sweeteners, plant fiber, corn sugar, conjugated sugars, curculigosin, cyclamates, cyclocaryoside I, demerara, dextran, dextrin, diastatic malt.malt), dulcin, sucrol, valzin, dulcogenin A, dulcogenin B, emulin, enoxolone, maltodextrin, saccharin, estragole, ethyl maltol, glucin, gluconic acid, gluconolactone, glucosamine, glucuronic acid, glycerol, glycyphillin, glycyrrhizin, glycyrrhetinic acid monoglucuronide, golden sugar, yellow sugar, golden syrup, granulated sugar, Gynostemma pentaphyllum, hernandulcin, isomerized liquid sugar, jallab, chicory root dietary fiber, kynurenine derivatives (including N'-formyl-kynurenine, N'-acetyl-kynurenine, 6-chloro-kynurenine), galactose Alcohol, litesse, ligicane, lycasin, N-(4-cyanophenyl)-N-(2,3-methylenedioxybenzyl)guanidinacetic acid, guanidine, farernum syrup, areca nut protein I, areca nut protein II, maltol, crystalline maltitol, maltodextrin, maltotriol, mannosamine, miraculin, mizuame, mogrosides (including, for example, mogroside IV, mogroside V and neomogroside), mukurozioside, nanosugar, naringin dihydrochalcone, neohesperidin dihydrochalcone, crude sugar (nib Sugar), black oligosaccharides, norbu, almond syrup, osladin, pekmez, pentadin, periandrin I, perillartine, petphyllum, phenylalanine, phloisosideside I, phlorodizin, phyllodulcin, polyglycitol syrup, polypodoside A, pterocaryoside A, pterocaryoside B, rebiana, refined syrup, rub syrup, rubusoside, selligueain A, shugr, sarmandin I, siraitiagrosvenorii, soybean oligosaccharides, Splenda, SRI oximeV, steviol glycosides, steviol disaccharides, steviol glycosides, strogins 1, 2 and 4, sucronic acid, sucrononate, sugars, sodium p-nitrophenylureapropionate (suosan), phloridzin, super aspartame, tetrasaccharides, threitol, treacle, trilobtain, tryptophan and its derivatives (6-trifluoromethyl-tryptophan, 6-chloro-D-tryptophan), vanilla sugar, heptenetropeol, beet syrup, aspartame-acesulfame potassium, assugrin, and any combination or blend of two or more of them.

[0037] In some embodiments, the flavor-modifying composition may comprise any other ingredients commonly used in the product or a combination of multiple ingredients, including but not limited to:

[0038] Acids, including, for example, citric acid, phosphoric acid, ascorbic acid, sodium bisulfate, lactic acid, or tartaric acid;

[0039] Bitter components include, for example, caffeine, quinine, green tea, catechins, polyphenols, Robusta coffee bean extract, coffee bean extract, potassium chloride, menthol, or proteins (such as proteins and protein isolates derived from plants, algae, or fungi).

[0040] Coloring agents, including, for example, caramel color, red #40, yellow #5, yellow #6, blue #1, red #3, purple carrot, black carrot juice, purple sweet potato, vegetable juice, fruit juice, beta-carotene, curcumin, or titanium dioxide;

[0041] Preservatives, including, for example, sodium benzoate, potassium benzoate, potassium sorbate, sodium metabisulfite, sorbic acid, or benzoic acid;

[0042] Antioxidants, including, for example, ascorbic acid, calcium disodium EDTA, α-tocopherol, mixed tocopherols, rosemary extract, grape seed extract, resveratrol, or sodium hexametaphosphate;

[0043] Vitamins or functional ingredients, including, for example, resveratrol, Co-Q10, omega-3 fatty acids, theanine, choline chloride (citocoline), cellulose, inulin (chicory root), taurine, ginseng extract, guarana extract, ginger extract, L-phenylalanine, L-carnitine, L-tartrate, D-glucuronide, inositol, bioflavonoids, echinacea, ginkgo biloba, yerba mate, flaxseed oil, Garcinia cambogia peel extract, white tea extract, ribose, milk thistle (milk) Thistle extract, grape seed extract, pyridoxine hydrochloride (vitamin B6), cyanocobalamin (vitamin B12), nicotinamide (vitamin B3), biotin, calcium lactate, calcium pantothenate (pantothenic acid), calcium phosphate, calcium carbonate, chromium chloride, chromium polynicotinate, copper sulfate, folic acid, ferric pyrophosphate, iron, magnesium lactate, magnesium carbonate, magnesium sulfate, monopotassium phosphate, monosodium phosphate, phosphorus, potassium iodide, potassium phosphate, riboflavin, sodium sulfate, sodium gluconate, sodium polyphosphate, sodium bicarbonate, thiamine mononitrate, vitamin D3, vitamin A palmitate, zinc gluconate, zinc lactate or zinc sulfate;

[0044] Clouding agents, including, for example, ester gum, brominated vegetable oil (BVO) or sucrose isobutyrate acetate (SAIB);

[0045] Buffer solutions, including, for example, sodium citrate, potassium citrate, or salts;

[0046] Flavorings (edible flavorings), including, for example, propylene glycol, ethanol, glycerin, gum arabic (acacia gum), maltodextrin, modified corn starch, dextrose, natural flavorings, natural flavorings containing other natural flavorings (WONF), natural and artificial flavorings, artificial flavorings, silicon dioxide, magnesium carbonate or tricalcium phosphate; or

[0047] Starch and stabilizers, including, for example, pectin, xanthan gum, carboxymethyl cellulose (CMC), polysorbate 60, polysorbate 80, medium-chain triglycerides, cellulose gel, cellulose gum, sodium caseinate, modified food starch, gum arabic (acacia gum), inulin, or carrageenan.

[0048] When dissolved or suspended in an aqueous medium, the flavor-modifying composition can have any suitable pH, ranging from low to neutral. Low and neutral pH values ​​include, but are not limited to, 1.5 to 9.0, or 2.5 to 8.5; 3.0 to 8.0; 3.5 to 7.5, and 4.0 to 7.

[0049] The ingestible composition according to any one of the foregoing embodiments may, in some embodiments, further include one or more additional flavor-modifying compounds, such as compounds that enhance sweetness (e.g., hesperidin, naringin, etc.), compounds that block bitterness, compounds that enhance umami, compounds that reduce sourness or licorice flavor, compounds that enhance saltiness, compounds that enhance cooling effects, or any combination thereof.

[0050] In some embodiments, the flavor-enhancing compositions disclosed herein comprise one or more sweetness-enhancing compounds. Such sweetness-enhancing compounds include, but are not limited to, naturally derived compounds such as hesperidin, naringenin, rhubarb glycoside, glucosylated steviol glycoside, glycyrrhizic acid derived from licorice, aromadendrin-3-O-acetate or other similar flavonols or flavonoids, or synthetic compounds such as those described in U.S. Patent Nos. 8,541,421; 8,815,956; 9,834,544; 8,592,592; 8,877,922; 9,000,054; and 9,000,051, and any compound described in U.S. Patent Application Publication No. 2017 / 0119032. Suitable examples include 3-((4-amino-2,2-dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2,2-dimethyl-N-propyl-propionamide, N-(1-((4-amino-2,2-dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2-methyl-prop-2-yl)isonicotinamide, or any combination thereof.

[0051] In some further embodiments, the flavor-enhancing compositions disclosed herein comprise one or more other umami or rich flavor-enhancing compounds. Such umami-enhancing compounds include, but are not limited to, naturally derived compounds, such as (E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenylethyl)acrylamide, or synthetic compounds, such as any of the compounds described in U.S. Patent Nos. 8,735,081; 8,124,121; and 8,968,708.

[0052] In some further embodiments, the flavor-enhancing compositions disclosed herein comprise one or more cooling-enhancing compounds. Such cooling-enhancing compounds include, but are not limited to, naturally derived compounds, such as menthol or analogues thereof, or synthetic compounds, such as any of the compounds described in U.S. Patent Nos. 9,394,287 and 10,421,727.

[0053] In some further embodiments, the flavor-modifying compositions disclosed herein comprise one or more bitterness-blocking compounds. Such bitterness-blocking compounds include, but are not limited to, naturally derived compounds, such as menthol or analogues thereof, or synthetic compounds, such as any of the compounds described in U.S. Patent Nos. 8,076,491; 8,445,692; and 9,247,759.

[0054] In some further embodiments, the flavor-modifying compositions disclosed herein comprise one or more taste-improving compounds. Such taste-improving compounds include, but are not limited to, tannins, cellulose materials, bamboo powder, etc.

[0055] In some further embodiments, the flavor-modifying compositions disclosed herein comprise one or more flavor-masking compounds. Such flavor-masking compounds include, but are not limited to, cellulose materials, materials extracted from fungi, materials extracted from plants, citric acid, carbonic acid (or carbonates), etc.

[0056] In some embodiments, the flavor-modifying compositions disclosed herein may contain cyclosal. When cyclosal is present, it is present at a relative concentration similar to that of oxacyclohexadecane-2-one.

[0057] Flavor-modifying compositions can be in any suitable form. For example, in some embodiments, the composition is in solid form, such as a solid powder. In some such embodiments, the composition also comprises a solid carrier, such as carbohydrates. In some other embodiments, the flavor-modifying composition is in the form of a liquid solution or suspension. This liquid form can be aqueous or non-aqueous, or it can be an emulsion, such as an oil-in-water or water-in-oil emulsion. In some embodiments, the flavor-modifying composition is incorporated into flavored products, such as oral care products, such as toothpaste or mouthwash.

[0058] In some embodiments, the flavor-modifying composition comprises one or more flavoring agents (edible flavorings / flavorings), or any other additives described in H. Mitchell, Sweeteners and Sugar Alternatives in Food Technology, Backwell Publishing Ltd., 2006. As used herein, the term "flavoring agent (edible flavoring)" includes those flavoring agents known to those skilled in the art, such as natural and artificial flavoring agents. These flavoring agents may be selected from synthetic flavoring oils and flavoring aromatic substances or from oils, oleoresins and extracts derived from plants, leaves, flowers, fruits, etc., and combinations thereof. Non-limiting representative flavoring oils include spearmint oil, cinnamon oil, wintergreen oil (methyl salicylate), peppermint oil, peppermint oil, clove oil, laurel oil, fennel oil, eucalyptus oil, thyme oil, cedarwood leaf oil, nutmeg oil, allspice, sage oil, mace, bitter almond oil, and cassia seed oil. Useful flavorings also include artificial, natural, and synthetic fruit flavorings, such as vanilla and citrus oils, including lemon, orange, lime, grapefruit, yuzu, and sudachi, as well as fruit flavorings, including apple, pear, peach, grape, blueberry, strawberry, raspberry, cherry, plum, pineapple, watermelon, apricot, banana, cantaloupe, plum, cherry, raspberry, blackberry, tropical fruit, mango, mangosteen, pomegranate, papaya, etc. Other potential flavorings include milk flavorings, butter flavorings, cheese flavorings, cream flavorings, and yogurt flavorings; vanilla flavorings; tea or coffee flavorings, such as green tea flavorings, oolong tea flavorings, tea flavorings, cocoa flavorings, chocolate flavorings, and coffee flavorings; mint flavorings, such as peppermint flavorings, spearmint flavorings, and Japanese mint flavorings; and spice flavorings, such as asafoetida flavorings, Indian fennel flavorings, anise flavorings, angelica flavorings, fennel flavorings, allspice flavorings, cinnamon flavorings, chamomile flavorings, mustard flavorings, cardamom flavorings, coriander flavorings, fennel flavorings, clove flavorings, pepper flavorings, cilantro flavorings, and sassafras flavorings. Seasonings include savory seasonings, Sichuan pepper seasonings, perilla seasonings, juniper berry seasonings, ginger seasonings, star anise seasonings, horseradish seasonings, thyme seasonings, tarragon seasonings, dill seasonings, bell pepper seasonings, nutmeg seasonings, basil seasonings, marjoram seasonings, rosemary seasonings, bay leaf seasonings, and mustard (Japanese horseradish) seasonings; alcoholic seasonings, such as red wine seasonings, whiskey seasonings, brandy seasonings, rum seasonings, gin seasonings, and liqueur seasonings; floral seasonings; and vegetable seasonings, such as onion seasonings, garlic seasonings, cabbage seasonings, carrot seasonings, celery seasonings, mushroom seasonings, and tomato seasonings. These seasonings can be used in liquid or solid form and can be used alone or in combination.Common flavorings include peppermint, such as peppermint, menthol, spearmint, artificial vanilla, cinnamon derivatives, and various fruit flavorings, whether used alone or in combination. Flavorings can also provide a fresh breath property, especially peppermint flavorings when used in combination with cooling agents.

[0059] Flavorings can also provide a fresh breath property, especially mint flavorings when used in combination with cooling agents. These flavorings can be used in liquid or solid form and can be used alone or in combination. Other useful flavorings include aldehydes and esters, such as cinnamyl acetate, cinnamaldehyde, citral diethyl acetal, dihydrocarboxyl acetate, eugenol formate, p-methyl anisole, etc. Generally, any flavoring or food additive can be used, such as those described by the National Academy of Sciences in Chemicals Used in Food Processing, publication 1274, pages 63-258.

[0060] Other examples of aldehyde flavoring agents include, but are not limited to, acetaldehyde (apple), benzaldehyde (cherry, almond), anisaldehyde (licorice, fennel), cinnamaldehyde (cinnamon), citral (α-citral, lemon, lime), neraldehyde (β-citral, lemon, lime), decanal (orange, lemon), ethyl vanillin (vanilla, cream), jasmine aldehyde (piperaldehyde, vanilla, cream), vanillin (vanilla, cream), α-pentylcinnamaldehyde (spicy fruit flavoring agent), butyraldehyde (butter, cheese), pentanal (butter, cheese), citronellol (modified products, various types), decanal (citrus fruits), aldehyde C-8 (citrus fruits), aldehyde C-9 (citrus fruits), aldehyde C-12 (citrus fruits), 2-ethylbutanal (berries), and hexenal (trans-2-ethylbutanal). (Berry), toluene formaldehyde (cherry, almond), veratral (vanilla), 2,6-dimethyl-5-hepten, i.e., melon aldehyde (melon), 2,6-dimethyloctaldehyde (green fruit), and 2-dodecenal (citrus, mandarin orange), cherry, grape, strawberry shortbread, and mixtures thereof. This list of flavorings is merely exemplary and is not intended to limit the scope of the term "flavoring" or the generally disclosed range.

[0061] In some embodiments, peppermint flavorings, including menthol and related compounds, or other breath-freshening compounds, may be combined with cooling agents, such as those described in U.S. Patent Nos. 9,394,287 and 9,732,071. Other examples of cooling agents include 5-methyl-2-(propane-2-yl)cyclohexyl-N-ethyloxane ester, N-ethyl-p-menthaneformamide (WS-3, also known as menthane-3-carboxylic acid-N-acetamide), N-2,3-trimethyl-2-isopropylbutyramide (WS-23), menthyl lactate (Frescolat.RTM. ML), and menthone glycerol acetal (Frescolat.RTM). MGA), menthyl succinate monomenthol (Physcool.RTM.), menthyl glutarate monomenthol, O-menthyl-glycerol, menthyl-N,N-dimethyl succinate, N-(4-cyanomethylphenyl)-p-menthanecarboxamide, N-(2-(pyridin-2-yl)ethyl)-3-p-menthanecarboxamide, menthol and menthol derivatives (e.g., L-menthol, D-menthol, racemic menthol, isomenthol, neoisomenthol, neomenthol), menthyl ethers (e.g., (1-menthoxy)-1,2-propanediol, (1-menthoxy)-2-methyl-1,2-propanediol, 1-menthyl-methyl ether), menthyl esters (e.g., menthyl formate, menthyl acetate, menthyl isobutyrate, menthyl lactate, L-menthyl-L-lactate, L-menthyl-D-lactate, menthyl-(2-methoxy)acetate, menthyl-(2-methoxyethoxy)acetate, menthyl pyroglutamic acid), N-(4-cyanomethylphenyl)-p-menthanecarboxamide, N-(2-(pyridin-2)-yl)ethyl)-3-p-menthanecarboxamide, menthyl carbonate (e.g., menthyl propylene glycol carbonate, menthyl ethylene glycol carbonate, menthyl glyceryl carbonate, or mixtures thereof), menthyl carboxylic acid amide (e.g., menthyl carboxylic acid-N-ethylamide [WS3], N-α).-(menthane-carbonyl)glycine ethyl ester [WS5], menthane carboxylic acid-N-(4-cyanophenyl)amide, menthane carboxylic acid-N-(alkoxyalkyl)amide), menthone and menthone derivatives (e.g., L-menthone glycerol ketal), 2,3-dimethyl-2-(2-propyl)-butyric acid derivatives (e.g., 2,3-dimethyl-2-(2-propyl)-butyric acid-N-methylamide [WS23]), isoprene alcohol or its esters (1-(-)-isomenthane alcohol, 1-(-)-isomenthane alcohol) Acetates), menthol derivatives (e.g., p-menthol-3,8-diol), N-(4-cyanomethylphenyl)-p-menthol formamide, N-(2-(pyridin-2-yl)ethyl)-3-p-menthol formamide, piperazine alcohol or synthetic or natural mixtures containing piperazine alcohol, pyrrolidone derivatives of cycloalkyl diones (e.g., 3-methyl-2-(1-pyrrolyl)-2-cyclopenten-1-one) or tetrahydropyrimidin-2-ones (e.g., icilin or related compounds, such as WO3). Menthol, N-(4-cyanomethylphenyl)-p-menthanecarboxamide, N-(2-(pyridin-2-yl)ethyl)-3-p-menthanecarboxamide, menthyl ethers (e.g., (1-menthoxy)-1,2-propanediol, (1-menthoxy)-2-methyl-1,2-propanediol), more polar menthyl esters (e.g., menthyl lactate, L-menthyl-L-lactate, L-menthyl-D-lactate, menthyl-(2-methoxy)acetate, menthyl-(2-methoxyethoxy)acetate, menthyl pyroglutamic acid ester), menthyl carbonates (e.g., menthyl propylene glycol carbonate, menthyl ethylene glycol carbonate, menthyl glycerol carbonate), and half-esters of menthol with dicarboxylic acids or their derivatives (e.g., succinic acid). Menthyl monomenthol, glutaric acid menthyl monomenthol, O-menthyl succinate-N,N-(dimethyl)amide, O-menthyl succinate amide), 3,4-methylenedioxycinnamic acid-N-cyclohexyl-N-2-pyridineamide, isopropyl-(5-methoxy-2-pyridin-2-yl-pyrimidin-4-yl)-amine, 3,4,6,7,11b,12-hexahydro-3,3-dimethyl-spiro[13H-dibenzo[a,f]quinazine-1-3,2'-[1,3]dithiacyclopentane]-1(2H)-one, 5,6,10b,11-tetrahydro-3-methyl-spiro[12H-benzo[a]furano[3,4-f]quinazine-1-2,2'-[1,3]dithiacyclopentane]-1(3H)-one. The most preferred cooling compounds are those selected from the group consisting of: 5-methyl-2-(propane-2-yl)cyclohexyl-N-ethyloxane ester, N-ethyl-p-menthaneformamide (WS-3, also known as menthane-3-carboxylic acid-N-ethylamide), menthyl lactate (Frescolat.RTM. ML), and menthone glycerol acetal (Frescolat.RTM).MGA), N-(4-cyanomethylphenyl)-p-menthaneformamide, and (1-menthoxy)-1,2-propanediol.

[0062] Uses, methods and flavored products

[0063] In at least another form, this disclosure provides the use of flavor-modifying compositions of the foregoing forms and embodiments thereof for reducing off-flavors in flavored products.

[0064] In related forms, this disclosure provides a method for reducing off-flavors in flavored products, the method comprising introducing a flavor-modifying composition of the aforementioned forms and embodiments thereof into the flavored product.

[0065] In connection with these forms, the flavored product can be any flavored product according to the forms and embodiments set forth below. In some embodiments, the flavored product is an oral care product, such as toothpaste, mouthwash, or teeth whitening composition, such as the composition disclosed in U.S. Patent Application Publication No. 2019 / 0167545, which is incorporated herein by reference.

[0066] In some embodiments, the flavored product contains an alkali metal salt of persulfate, such as potassium persulfate. In embodiments where the flavor-modifying composition of the foregoing form is incorporated into or introduced into the flavored product, its concentration is such that the total concentration of all components of classes (a), (b), (c), and (d) ranges from 10 ppm to 4000 ppm, or 20 ppm to 3000 ppm, or 30 ppm to 2500 ppm, or 50 ppm to 2000 ppm, or 100 ppm to 1500 ppm, wherein “ppm” is based on the total weight of the flavored product on a weight / weight basis. In embodiments where only (a) and (b) are present, the concentration is adjusted accordingly, for example, from 10 ppm to 800 ppm, or 20 ppm to 600 ppm, or 30 ppm to 500 ppm, or 50 ppm to 400 ppm, or 100 ppm to 300 ppm, wherein “ppm” is based on the total weight of the flavored product on a weight / weight basis.

[0067] In embodiments containing an alkali metal salt of persulfate, such as potassium persulfate, the concentration ratio (w / w) of the alkali metal salt of persulfate to the sum of all components of classes (a), (b), (c), and (d) ranges from 25:1 to 10,000:1, or 50:1 to 8,000:1, or 100:1 to 7,000:1, or 200:1 to 6,000:1. Other non-limiting examples of alkali metal salts of persulfate include lithium persulfate and sodium persulfate.

[0068] In some embodiments, additional salt may also be present in the flavored product. For example, in some embodiments, the flavored product contains potassium bisulfate and potassium sulfate.

[0069] Flavored products can be in any suitable physical form. For example, in some embodiments, the flavor-modifying composition can be in solid form, such as a powder. In another such embodiment, the flavored product is a tooth powder, such as a tooth powder used for whitening teeth, removing stains (e.g., tobacco stains), etc. In some other embodiments, the flavored product can be a paste or slurry, such as toothpaste. In some other embodiments, the flavored product can be in the form of a cream or gel, such as a tooth gel, skin cream, or tooth cream. In some other embodiments, the flavored product can be, for example, a liquid suspension or solution having an aqueous carrier. In some embodiments, the flavored product can be in the form of an emulsion, such as a microemulsion or nanoemulsion, in which surfactants, emulsifiers, etc., may be present. In some embodiments, the flavored product is a personal care product, such as a product for application to the skin, face, lips, gums, mouth, etc. Such personal products can be used for any suitable purpose, such as skin whitening, teeth whitening, etc.

[0070] In some forms, this disclosure provides flavored products comprising any composition of the foregoing forms or embodiments thereof.

[0071] In some implementations, the flavored product is an oral care product. "Oral care product" refers to a personal care product or other product that, during normal use, is not intended to be swallowed for the purpose of systemic application of a specific therapeutic agent, but rather remains in the mouth for a sufficient duration to contact substantially all tooth surfaces and / or oral tissues for oral activities. Oral care compositions can take many forms, including toothpaste, dental floss, teething gel, subgingival gel, mouthwash, mousse, foam, oral spray, lozenges, chewing tablets, chewing gum, or denture products. Oral care compositions may also be incorporated into strips or films for direct application or adhesion to oral surfaces.

[0072] The flavored product according to any one of the foregoing embodiments may, in some embodiments, further include one or more additional flavor-modifying compounds, such as compounds that enhance sweetness (e.g., hesperidin, naringin, glucosylated steviol glycosides, etc.), compounds that suppress bitterness, compounds that enhance umami, compounds that reduce acidity, compounds that enhance saltiness, compounds that enhance cooling effects, or any combination thereof.

[0073] In some embodiments of any form and implementation of a sweetener or flavoring concentrate described herein, the sweetener or flavoring concentrate is a non-naturally occurring product, such as a composition specifically manufactured for the production of a flavored product.

[0074] In one embodiment, the flavor concentrate comprises: i) a compound disclosed and described herein, alone or in combination; ii) a carrier; and iii) optionally, at least one adjuvant. The term "carrier" refers to a generally inactive auxiliary substance, such as a solvent, binder, or other inert medium, used in combination with the compounds of the present invention and one or more optional adjuvants to form a formulation. For example, water or starch can be a carrier for a flavor concentrate formulation. In some embodiments, the carrier is the same as the dilution medium used to reconstitute the flavor concentrate formulation; in other embodiments, the carrier is different from the dilution medium. As used herein, the term "carrier" includes, but is not limited to, an intake-acceptable carrier.

[0075] The term "adjuvant" refers to an additive that complements, stabilizes, maintains, or enhances the intended function or efficacy of an active ingredient, such as the compounds of the present invention. In one embodiment, at least one adjuvant comprises one or more flavoring agents. Flavoring agents may have any flavor known to those skilled in the art or to consumers, such as chocolate, coffee, tea, mocha, French vanilla, peanut butter, chai, or combinations thereof. In another embodiment, at least one adjuvant comprises one or more sweeteners. The one or more sweeteners may be any sweetener described in this application. In yet another embodiment, the at least one adjuvant comprises one or more ingredients selected from the group consisting of: emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, salts, and combinations thereof. Examples of emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, and salts are described in U.S. Patent No. 6,468,576, the entire contents of which are incorporated herein by reference in their entirety for all purposes.

[0076] In one embodiment, the flavor concentrate formulation of the present invention may be in the form of liquids, solids, foam materials, pastes, gels, emulsions, and combinations thereof, including solutions and suspensions, such as liquids containing a certain amount of solid contents. In one embodiment, the flavor concentrate formulation is in the form of a liquid, including both water-based and non-water-based formulations. In some embodiments, the flavor concentrate formulation of the present invention may be carbonized or non-carbonated.

[0077] Flavor concentrate formulations may further comprise a freezing point depressant, a nucleating agent, or both as at least one adjuvant. A freezing point depressant is an intake-acceptable compound or reagent that lowers the freezing point of a liquid or solvent to which the compound or reagent is added. That is, the freezing point of a liquid or solution containing a freezing point depressant is lower than the freezing point of a liquid or solvent without a freezing point depressant. In addition to lowering the initial freezing point, a freezing point depressant may also lower the water activity of the flavor concentrate formulation. Examples of freezing point inhibitors include, but are not limited to, carbohydrates, oils, ethanol, polyols such as glycerol, and combinations thereof. A nucleating agent refers to an intake-acceptable compound or reagent capable of promoting nucleation. Examples of nucleating agents include, but are not limited to, calcium silicate, calcium carbonate, titanium dioxide, and combinations thereof.

[0078] In some embodiments, the flavor concentrate formulation is formulated to have a low water activity to extend shelf life. Water activity is the ratio of the vapor pressure of water in the formulation to the vapor pressure of pure water at the same temperature. In one embodiment, the water activity of the flavor concentrate formulation is less than about 0.85. In another embodiment, the water activity of the flavor concentrate formulation is less than about 0.80. In yet another embodiment, the water activity of the flavor concentrate formulation is less than about 0.75.

[0079] Example

[0080] To further illustrate the invention, the following embodiments are included. These embodiments should not be construed as specifically limiting the invention. Variations of these embodiments within the scope of the claims are within the capabilities of those skilled in the art and are considered to fall within the scope of the invention described and claimed herein. The reader will recognize that those skilled in the art, upon mastering this disclosure, can prepare and use the invention without exhaustive examples.

[0081] Example 1 – Toothpaste Formulation Sample

[0082] According to certain embodiments of this disclosure, toothpaste formulations incorporating flavor-modifying compositions have been prepared. Table 1 below lists the ingredients contained in the flavor-modifying compositions and their recommended concentrations when incorporated into toothpaste.

[0083] Table 1

[0084]

[0085] *Glucosylated natural steviol glycoside is PureCircle's GSG NSF-02, which has a glucosylation degree of 2.36 and contains α-1,6 bonds.

[0086] Please note that the labels for the four ingredients listed above are from (A) to (D). Table 2 below shows several alternative embodiments of the toothpaste formulation that can be prepared. The amounts are reported as a weight percentage based on the total weight of the toothpaste composition. Please note that other ingredients are labeled as follows.

[0087] (E)WNQ-14-001 Toothpaste Base

[0088] (F) Potassium persulfate

[0089] (G) Peppermint flavoring

[0090] (H) Sodium saccharin

[0091] Table 2

[0092]

[0093] Example 2 – Sensory Testing

[0094] A group of sensory testers tested various compositions. Each of the test compositions T1 and T2 was tested by a panel member, who was asked to rate its odor on a scale of 1 to 5, where 5 was equivalent to composition T1, and 1 had no odor at all. Table 3 shows the results.

[0095] Table 3

[0096] .

Claims

1. A taste-modifying composition for reducing odor perception associated with alkali metal salts of persulfate in oral care products, comprising: (a) 4-amino-5,6-dimethylthiopheno[2,3-d]pyrimidine-2(1H)-one, or a salt thereof; and (b) a lactone, wherein the lactone is dihydromenthene lactone, and the composition comprising (c) a glucosylated natural steviol glycoside and (d) a sweetener, wherein the sweetener is sucralose. The weight-to-weight ratio of compounds (a) and (b) is in the range of 2:1 to 4:

1. The weight-to-weight ratio of compounds in class (a) and (c) is in the range of 1.2:1.0 to 2.0:1.

0. The weight-to-weight ratios of compounds in categories (b) and (c) are in the range of 1:3 to 1:

1. The weight-to-weight ratio of compounds in class (a) and class (d) is in the range of 1:8 to 1:

4. The weight-to-weight ratio of compounds in categories (b) and (d) is in the range of 1:30 to 1:12, and The weight-to-weight ratio of compounds in class (c) and class (d) is in the range of 1:20 to 1:

5.

2. The flavor-improving composition according to claim 1, further comprising menthol.

3. The flavor-enhancing composition according to claim 1, further comprising a cooling-enhancing compound, wherein the compound is selected from the group consisting of: N-Ethyl-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide; N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-2-(p-tolyloxy)acetamide; 2-(4-fluorophenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)acetamide; 2-(2-hydroxy-4-methylphenoxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-acetamide; 2-((2,3-dihydro-1H-inden-5-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-acetamide; 2-((2,3-dihydro-1H-inden-5-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiazolyl-5-ylmethyl)-acetamide; and 2-((5-methoxybenzofuran-2-yl)oxy)-N-(1H-pyrazol-3-yl)-N-(thiophen-2-ylmethyl)-acetamide.

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